4-(ethoxycarbonylmethyl)phenylboronic acid, pinaco Chemical Properties

Boiling point:

377.7±25.0 °C(Predicted)

Density 

1.06±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

clear liquid

color 

Colorless to Light yellow to Light orange

Safety Information

HS Code 

2931900090

4-(ethoxycarbonylmethyl)phenylboronic acid, pinaco Usage And Synthesis

Uses

4-Ethoxycarbonylmethylphenylboronic acid, pinacol ester

Synthesis

GENERAL STEPS: Ethyl (4-bromophenyl)acetate (100 g, 411 mmol), bis(pinacolato)diboron (125.4 g, 493.7 mmol), and potassium acetate (125.4 g, 493.7 mmol) were added to a 2L round bottom flask. 1,4-dioxane (1 L) was added and stirred under nitrogen protection for 15 min. Subsequently, [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane complex (3.36 g, 4.11 mmol) was added, and the reaction mixture was heated in an oil bath at 100 °C for 2 hours. The reaction process was monitored by analytical HPLC. After completion of the reaction, 1,4-dioxane was removed by concentration under reduced pressure and the residue was dissolved in ethyl acetate. The solution was filtered through a silica gel column (6 x 4 in.) and ethyl acetate (1.5 L) was used as eluent to afford ethyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate (117 g, 98% yield).1H NMR (400 MHz, DMSO) δ ppm: 7.63 (d, 2H, J=8 Hz). 7.27 (d, 2H, J=8Hz), 4.07 (q, 2H, J=7Hz), 3.68 (s, 2H), 1.28 (s, 12H), 1.16 (t, 3H, J=7Hz).

References

[1] Patent: WO2006/86609, 2006, A2. Location in patent: Page/Page column 152-153
[2] Patent: US2014/206686, 2014, A1. Location in patent: Paragraph 0452-0454
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7920 - 7939,20
[4] Patent: WO2013/189865, 2013, A1. Location in patent: Page/Page column 30
[5] Patent: US2012/295874, 2012, A1. Location in patent: Page/Page column 230

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